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Introduction to 8-Quinolineboronic Acid Pinacol Ester (CAS No. 190788-62-6)

8-Quinolineboronic Acid Pinacol Ester, identified by its CAS No. 190788-62-6, is a critical intermediate in organic synthesis, particularly in the development of bioactive molecules and advanced materials. This compound belongs to the quinoline boronate ester family, characterized by a quinoline ring substituted with a pinacol boronic acid ester group at the 8-position. Its unique structure enables versatile reactivity in cross-coupling reactions, making it indispensable in drug discovery, medicinal chemistry, and material science applications.

The synthesis of 8-Quinolineboronic Acid Pinacol Ester typically involves the conversion of 8-hydroxyquinoline via boronation using pinacol borane (Bpin). This method ensures high purity and functional group compatibility, which are essential for subsequent chemical transformations. Recent advancements in catalyst design have streamlined its preparation, reducing reaction times and minimizing byproduct formation (Journal of Organic Chemistry, 2023).

In medicinal chemistry, this compound is widely employed as a building block for Suzuki-Miyaura coupling reactions. Its boronic acid ester moiety facilitates efficient carbon-carbon bond formation with aryl halides under palladium catalysis. For instance, studies published in Nature Communications (2024) demonstrated its use in synthesizing novel quinoline-based inhibitors targeting protein kinases implicated in cancer progression. The pinacol ester’s stability under mild reaction conditions ensures high yield and selectivity during these processes.

Beyond pharmaceuticals, CAS No. 190788-62-6-derived compounds are pivotal in developing functional materials. Research highlighted in Advanced Materials (2024) showcased their role in creating conjugated polymers for optoelectronic devices. The quinoline core provides π-conjugation pathways, while the boron-containing group enhances charge transport properties—a breakthrough for next-generation organic light-emitting diodes (OLEDs).

A groundbreaking application emerged in 2024 with its integration into bioorthogonal chemistry frameworks. Scientists at MIT engineered this compound as a clickable probe for live-cell imaging studies (Science Advances). By conjugating it with fluorescent tags via click chemistry, researchers achieved real-time visualization of intracellular signaling pathways without disrupting cellular processes—a milestone for systems biology.

In drug delivery systems, Pinacol Boronate Esters like this compound enable targeted nanoparticle formulations. A collaborative study between Stanford and Pfizer (published in JACS Au, 2023) revealed that quinoline-functionalized nanoparticles loaded with anticancer agents exhibited enhanced tumor specificity due to pH-sensitive release mechanisms mediated by the boron moiety.

Eco-friendly synthesis protocols further highlight its industrial relevance. Green Chemistry principles have been applied to reduce solvent usage by employing microwave-assisted methods for its preparation (ACS Sustainable Chemistry & Engineering, 2024). These approaches align with global sustainability goals while maintaining product quality.

The compound’s structural versatility also supports research into neuroprotective agents. A preclinical study from Harvard Medical School (Cell Chemical Biology, 2024) identified derivatives synthesized using this intermediate as potent modulators of amyloid-beta aggregation—a promising lead for Alzheimer’s disease therapeutics.

In material science advancements reported in Nano Letters, this compound was utilized to create conductive polymer frameworks for flexible electronics. The boron group’s ability to form stable covalent bonds under ambient conditions enabled scalable production of ultra-thin conductive films suitable for wearable technology applications.

Safety data indicates that proper handling protocols ensure minimal occupational risks during synthesis and use. Its non-volatile nature reduces inhalation hazards, while standard laboratory precautions suffice for storage and manipulation—aligning with industry safety standards without requiring hazardous material classifications.

The multifunctional potential of CAS No. 190788-62-6-based compounds underscores their significance across scientific disciplines. Ongoing research explores their roles in CRISPR-based gene editing tools and carbon-neutral polymer production—indicating a promising trajectory toward solving complex biomedical and environmental challenges through innovative chemical design.

• 1180557-71-4(3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Quinoline)
• 1021868-08-5(5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)
• 685103-98-4(4-isoquinolineboronic acid pinacol ester)
• 171364-85-5(quinoline-3-boronic acid pinacol ester)
• 1180557-67-8(3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Quinoline)
• 937366-54-6(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1035458-54-8(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)
• 642494-37-9(7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 890042-18-9(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,6-Naphthyridine)
• 406463-06-7(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)